My sister is a year older than I am, she's seventeen, but she's two years ahead of me in school, and she had gotten a babysitting client from a girl she had known who was now away at college. The people, Holt and Dianne, were quite well off, lived in a big house in a gated part of our town and my sis always talked about how generously they paid her to babysit their two boys.
They asked her to babysit on a Friday night and she had to tell them that she was going away with the girl's soccer team and could I sit for them if I wasn't busy. They said yes and I said yes, so I drove over at six-thirty on Friday evening.
Well, as I pulled up in front, I must say, their house was pretty posh, looked kind of like a big house in France or something.
Dianne showed me in and around, nice big family room, big screen TV, DVD setup, the whole works. She also introduced me to her kids, they seemed nice and well-behaved, a blessing in my book. And, Dianne, herself, was pretty nice, petite, about five feet tall, blond hair to her shoulders, nice boobs, not too big, not too small, nice legs under her short skirt. Nice.
As she showed me around, I was mostly interested in her, her boobs, legs, ass, nice ass, I must tell you. Two or three times I think she kind of figured I was checking her out and got a little smile, then she would continue on.
After they left, I set up a movie for the boys and went off to further explore the house. In her bedroom, there were several pictures of Dianne and as I looked at each one, thoughts of her naked and me fucking her on her bed drifted through my mind. Hell, I'm sixteen, that's to be expected.
A while later one of the boys asked for a specific Disney movie, The Lion King, that I couldn't seem to find with the others. He suggested looking in their Mom's dresser in the master bedroom so I went down the hall and began to rummage through the drawers. In the interest of truth, I did get sidetracked a bit in her panty drawer, she had some wild thongs that got me hard as a rock and one pair of panties had written on it "Insert your cock here" and an arrow pointing to the crotch which had an opening in it. I liked this woman. Oh, yeah.
I finally tore myself away from her panty drawer and found a videotape in the back of one drawer under some nighties. Pulling it out, it read, "For Holt's Eyes Only." Oh, now this is interesting.
I soon got the boys to bed and fired up the tape on their bedroom setup. It was a video of Dianne in a sexy, low-cut dress. She was slowly dancing to some slow music in the background, moving her hips around and making my dick hard as a rock.
I stopped the tape and went down the hall to make sure the boys were asleep then went back and hit, 'play.' Soon, Dianne was stepping out of the dress and dancing in her bra and panties and I now had my pants around my ankles jacking-off. As she took off the bra and pulled down her panties, she went over to the bed, got up with her back against the headboard, reached over and got a vibrator out of the bed stand, spread her legs wide and began rubbing it all around and in and out of her pussy as I unloaded my cum all over the floor.
Just then I heard one of the boys, paused the tape and pulled my pants up to go check. After I looked in on the boys, I was quickly back watching the tape as she was running the vibrator in and out and all around her pussy and moaning and saying, 'I want your cock, Holt, come fuck my hot, wet pussy.'
Whew! I blew more cum onto the floor, then heard a noise, shut off the tape, pulled up my pants and went to see what it was. Turned out nothing, so I went back in, got a towel from the bathroom and wiped up all my cum from their nice hardwood floor. I rewound the tape and carefully put it back where I had found it. Just in time, too, they came back a few minutes after that.
I tried to look bored and I guess it worked. I got my pay (generous as my sister had said) and left for home. With another hard-on.
On Sunday, Dianne called me and asked if I could come sit for the kids for the afternoon. Figuring it was good money and maybe a chance to watch the video again, I quickly assented and drove right over. Dianne answered the door and let me in. I was rather stunned as she was wearing a bikini, a rather skimpy one at that.
"Come in Sean, come in. Good, just follow me," and I followed her beautiful ass down the hall and into her bedroom. As I stood there, trying to minimize the bulge in my pants, she open a dresser drawer, THE dresser drawer, and pulled out the video tape.
My hard-on vanished. My face turned red hot and I thought that they must have a security camera in the bedroom.
"Have you been in my dresser?"
"Um, well, I was looking for a Disney tape one of the boys wanted to watch. I couldn't find it."
Her face relaxed a bit and she asked, "Did you watch this tape, Sean?"
"Um, well, uh, yeah, I kind of did. I didn't know what it was and I promise I'll never ever tell anyone about it."
She sat down on the bed, held the tape up and said, "Did you enjoy it?"
"Um, well, yeah, I did. A lot. I'm sorry."
"Did you masturbate on one of my towels?"
Oh, shit. I put the towel in the dirty clothes in the laundry room. How did she know?
"Oh, um, yeah, I kind of did."
"Well, I found it in the laundry room and knew that I hadn't put it there. I opened it and there was your stuff inside. I know what semen looks like, Sean."
"Did my sons see any of this?"
"Oh, no, ma'am, no, oh, no. None of it. I swear."
"I'm glad of that, Sean."
"Oh, please don't quit using my sister to babysit because of what I've done. I'm really sorry and it's not her fault."
"Yes, you're right. This won't change us using her as a babysitter."
"Oh, thank you, thank you."
"Did you like what you saw on the tape?"
There's a question I wasn't expecting.
"Um, well, I, uh, yes, yes, I did. You are the most beautiful woman I've ever seen. Ever."
She patted the space next to her and I went over and sat down beside her.
"Did you watch all of it?"
"Um, no, I got scared that you two would come home and I turned it off."
She laughed and said, "Yeah, after you cummed all over one of my good towels."
She laughed again and asked, "Sean, do you have a girlfriend?"
"Yeah, for about six months now."
"Have you fucked her?"
"Well, no, she will let me, um, well, put my finger inside but that's all."
"Would you like to fuck me?"
Stunned, that's what I was. And confused. Was this a trick?
She stood up and reached back and undid her bikini top and let it fall to the floor and just stood there in front of me. She had nice sized breasts, not big ones or anything, but really nice with small, dark red nipples that were sticking out. She Stepped toward me and sat down facing me on my leg and led a nipple to my mouth.
"Suck nice and easy, Sean. Nice and slow."
I had sucked my girlfriend's nipples before and it was one of my favorite things. I could do it just forever.
She was breathing heavily and began to moan and arched her back and started to rub and hump against my thigh. Her nipple slipped out of my mouth and she immediately pushed her chest forward for me to suck her again as she humped back and forth on my leg.
"Oh, Sean, you make my tits so happy. Just don't stop. Suck my tits."
.... There is more of this story ...